3(2H)-furanone derivatives

ABSTRACT

The present invention relates to 3(2H)-furanone compounds possessing fungicidal activity to plant fungi and a process for preparing them.

This application is a 371 of PCT/KR95/00083 filed Jun. 30, 1995.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to novel 3(2H)-furanone derivatives of thefollowing formula (I) useful as fungicides having excellent activitiesto plant fungi and a process for preparing them. ##STR1## wherein, R isC₁ ˜C₂ alkyl, allyl or 2-chloroallyl group;

X is halogen atom, methyl, C₁ ˜C₂ alkoxy, cyano, thioethyl or nitrogroup; and

Y is halogen atom, hydrogen, methyl or trifluoromethyl group.

2. Description of the Prior Art

Prior to the present invention, furanone derivatives of the followingformula (a) were known as herbicides, but the compounds (a) had not beenused as fungicides. ##STR2## wherein, R¹ is alkyl group; and

A and B are independently halogen atom, trifluoromethyl or alkyl group.

SUMMARY OF THE INVENTION

The object of this invention is to provide novel 3(2H)-furanonecompounds of the above formula(I) which have a preventive effect againstvarious kinds of plant fungi, in particular which have selectivelyexcellent fungicidal activities to specific plant fungi.

Another object of this invention is to provide novel fungicidalcomposition comprising one or more compounds of the above formula(I) asan effective ingredient in combination with an inert carrier.

The present invention relates to 3(2H)-furanone derivatives of theformula(I). ##STR3## wherein, R, X and Y are respectively defined asdescribed previously.

DETAILED DESCRIPTION OF THE INVENTION

According to the present invention, 3(2H)-furanone derivatives of theformula (I) are novel compounds, and have an excellent preventive andfungicidal effect against plant fungi, in particular against rice sheathblight, cucumber gray mold, etc. Therefore, the derivatives are usefulas an agricultural and floricultural fungicide ingredient.

In the present invention, 3(2H)-furanone derivatives of the formula(I)may be prepared by the following reaction scheme. ##STR4##

In the above reaction scheme, X, Y and R are respectively defined asdescribed previously.

According to the above reaction scheme, N-oxide compound of theformula(II) prepared by the well-known process is converted intochloropyridine by treating with p-toluenesulfonyl chloride and then itwas reacted with potassium cyanide(KCN) in dimethyl sulfoxide(DMSO) toobtain cyanopyridine compound of the formula(III).

The obtained cyanopyridine compound(III) is reacted withhydroxymethylaromatic acid ester compound of the formula(IV) in thepresence of a base to prepare aminofuranone of the formula(V). Asubstituent is introduced at the position of amino group of theformula(V) by reacting with an alkyl or alkenyl halide compound in thepresence of a phase transfer catalyst to obtain the desired3(2H)-furanone derivatives of the formula(I).

According to the present invention, sodium methoxide(NaOMe) maypreferably be used as a base, and tetrabutylammonium bromide maypreferably be used as a phase transfer catalyst.

In the above formula(I), it may be the preferable compound that X and Rare respectively methyl group and Y is chlorine atom.

New compounds of the formula(I) prepared by the present invention maytypically be listed in following Table 1. ##STR5##

                                      TABLE 1    __________________________________________________________________________    Compound    No.   X     R        Y    mp(°C.)                                   .sup.1 H NMR(ppm)    __________________________________________________________________________    1     4-CH.sub.3                CH.sub.3 H         2.37(s, 3H), 3.20(s, 3H), 5.33                                   (s, 1H), 6.80˜8.17(m, 8H),                                   10.23(s, 1H)    2     4-CH.sub.3                CH.sub.2 CH.sub.3                         H         1.30(t, 3H), 2.27(s, 3H), 3.55                                   (q, 2H), 5.43(s, 1H), 6.67˜                                   8.17(m, 8H), 10.17(s, 1H)    3     4-CH.sub.3                CH.sub.2 --CH═CHCl                         H         2.36(s, 3H), 4.30(q, 2H), 5.90                                   (s, 1H), 6.13(m, 2H), 6.85˜                                   8.27(m, 8H), 10.55(s, 1H)    4     4-CH.sub.3                CH.sub.2 --CH═CH.sub.2                         H         2.27(s, 3H), 4.13(t, 2H), 5.06,                                   5.23(m, 3H), 5.43(s, 1H),                                   6.67˜8.07(m, 8H), 10.33(s,                                   1H)    5     4-CH.sub.3                CH.sub.2 --CH═CHCl                         4-CH.sub.3                                   2.34(s, 3H), 2.37(s, 3H),                                   4.30(m, 2H), 5.53(s, 1H),                                   6.17(m, 2H), 6.70˜8.23(m,                                   7H), 10.46(s, 1H)    6     4-CH.sub.3                CH.sub.3 4-CH.sub.3                                   2.30(s, 3H), 2.33(s, 3H), 3.17                                   (s, 3H), 5.53(s, 1H), 6.7˜                                   8.30(m, 7H), 10.23(s, 1H)    7     4-CH.sub.3                CH.sub.3 3-CH.sub.3                                   2.30(s, 3H), 2.33(s, 3H), 3.17                                   (s, 3H), 5.43(s, 1H), 6.73˜                                   8.23(m, 7H), 10.17 (s, 1H)    8     4-CH.sub.3                CH.sub.2 --CH═CHCl                         3-CH.sub.3                                   2.30(s, 3H), 2.33(s, 3H), 4.23                                   (m, 2H), 5.53(s, 1H), 6.17(m,                                   2H), 6.77˜8.30(m, 7H),                                   10.80(s, 1H)    9     4-CH.sub.3                CH.sub.3 2-F       2.36(s, 3H), 3.13(s, 3H), 5.85                                   (s, 1H), 6.77˜8.30(m, 7H),                                   10.30(s, 1H)    10    4-CH.sub.3                CH.sub.2 --CH═CHCl                         2-F       2.33(s, 3H), 4.33(m, 2H),                                   5.80(m, 1H), 6.17(m, 2H),                                   6.77˜8.23(m, 7H), 10.47(s,                                   1H)    11    4-CH.sub.3                CH.sub.3 4-F       2.34(s, 3H), 3.15(s, 3H), 5.78                                   (s, 1H), 6.78˜8.43(m, 7H),                                   10.38(s, 1H)    12    4-CH.sub.3                CH.sub.2 CH═CHCl                         3-F       2.30(s, 3H), 4.27(m, 2H),                                   5.47(s, 1H), 6.07(m, 2H),                                   6.76˜8.26(m, 7H),                                   10.50(s, 1H)    13    4-CH.sub.3                CH.sub.2 CH═CHCl                         4-F       2.34(s, 3H), 4.22(m, 2H),                                   5.48(s, 1H), 6.76˜8.29(m,                                   7H), 10.51(s, 1H).    14    4-CH.sub.3                CH.sub.2 CH═CHCl                         2-CF.sub.3                                   2.33(s, 3H), 4.23(m, 2H),                                   5.97(s, 1H), 6.07(m, 2H),                                   6.83˜8.30(m, 7H),                                   10.43(s, 1H)    15    4-CH.sub.3                CH.sub.3 2-CF.sub.3                                   2.60(s, 3H), 3.17(s, 3H), 5.97                                   (s, 1H), 6.93˜8.57(m, 7H),                                   10.33(s, 1H)    16    4-CH  CH.sub.3 3-CF.sub.3                                   2.30(s, 3H), 3.20(d, 3H), 5.53                                   (s, 1H), 6.70˜8.30(m, 7H)    17    4-CH.sub.3                CH.sub.2 CH═CHCl                         2-Cl      2.33(s, 3H), 4.21(m, 2H),                                   5.50(s, 1H), 6.07(m, 2H),                                   6.76˜8.30(m, 7H), 10.53(s,                                   1H)    18    4-CH  CH.sub.3 2-Cl      2.37(s, 3H), 3.17(s, 3H), 6.06                                   (s, 1H), 6.80˜8.23(m, 7H),                                   10.25(s, 1H)    19    4-CH.sub.3                CH.sub.2 CH.sub.3                         2-Cl      1.30(t, 3H), 2.30(s, 3H), 3.50                                   (q, 2H), 6.00(s, 1H), 6.80˜                                   8.20(m, 7H), 10.27(s, 1H)    20    4-CH.sub.3                CH.sub.2 CH═CHCl                         2-Cl      2.33(s, 3H), 4.30(q, 2H), 5.50                                   (s, 1H), 6.26(m, 2H), 6.76˜                                   8.30(m, 7H), 10.57(s, 1H)    21    4-CH.sub.3                CH.sub.3 4-C1      2.37(s, 3H), 3.23(s, 3H), 5.53                                   (s, 1H), 6.80˜8.30(m, 7H),                                   10.33(s, 1H)    22    4-CH.sub.3                CH.sub.2 CH═CHCl                         4-Cl      2.30(s, 3H), 4.33(m, 2H),                                   5.50(s, 1H), 6.10(m, 2H),                                   6.74˜8.27(m, 7H),                                   10.60(s, 1H)    23    4-CH.sub.3                CH.sub.3 2,4-Cl.sub.2                                   2.33(s, 3H), 3.23(s, 3H), 6.00                                   (s, 1H), 6.76˜8.30(m, 7H),                                   10.33(s, 1H)    24    4-CH.sub.3                CH.sub.2 CH═CHCl                         2,4-Cl.sub.2                                   2.33(s, 3H), 4.30(m, 2H), 5.9                                   (s, 1H), 6.07(m, 2H), 6.77˜                                   8.27(m, 7H)    25    4-CH.sub.3                CH.sub.3 3-Cl      2.30(s, 3H), 3.20(s, 3H), 5.47                                   (s, 1H), 6.80˜8.30(m, 7H),                                   10.30(s, 1H)    26    4-Cl  CH.sub.3 2-Cl      3.13(d, 3H), 5.93(s, 1H), 6.84˜                                   8.20(m, 7H), 9.76(s, JH)    27    4-Cl  CH.sub.2 CH.sub.3                         2-Cl      1.30(t, 3H), 3.50(q, 2H), 5.87                                   (s, 1H), 6.80˜8.37(m, 7H),                                   9.75(s, 1H)    28    4-Cl  CH.sub.2 CH═CHCl                         2-Cl      4.37(t, 2H), 5.93, 6.06(m,                                   2H), 7.03˜8.57(m, 7H),                                   10.13(s, 1H)    29    4-Cl  CH.sub.3 2-CF.sub.3                                   3.17(d, 3H), 5.97(s, 1H), 6.93˜                                   8.27(m, 7H), 10.00(s, H)    30    4-Cl  CH.sub.3 3-CF.sub.3                                   3.17(d, 3H), 5.53(s, 1H), 6.85˜                                   8.37(m, 7H), 9.90(s, 1H)    31    4-Cl  CH.sub.3 3-Cl      3.27(d, 3H), 5.54(s, 1H), 7.00˜                                   8.40(m, 7H), 10.20(s, 1H)    32    4-Cl  CH.sub.3 2,4-Cl.sub.2                                   3.17(d, 3H), 6.00(s, 1H), 6.97˜                                   8.53(m, 6H), 9.94(s, 1H)    33    4-Cl  CH.sub.3 4-CH.sub.3                                   2.38(s, 3H), 3.20(d, 3H), 5.47                                   (s, 1H), 6.90˜8.30(m, 7H),                                   9.87(s, 1H)    34    4-Br  CH.sub.3 2-Cl      3.10(d, 3H), 6.00(s, 1H), 6.97˜                                   8.47(m, 7H), 10.13(s, 1H)    35    4-Br  CH.sub.2 CH═CHCl                         2-Cl      4.33(t, 2H), 5.83, 6.10(m,                                   2H), 6.10(s, 1H), 6.93˜8.47                                   (m, 7H), 10.13(s, 1H)    36    4-Br  CH.sub.3 3-Cl      3.27(s, 3H), 5.60(s, 1H), 7.40˜                                   8.47(m, 7H), 10.05(s, 1H)    37    4-Br  CH.sub.3 2,4-Cl.sub.2                                   3.23(s, 3H), 6.03(s, 1H), 7.03˜                                   8.47(m, 6H), 10.05(s, 1H)    38    4-Br  CH.sub.3 2-CF.sub.3                                   3.17(d, 3H), 5.93(s, 1H), 6.90˜                                   8.50(m, 7H), 9.93(s, 1H)    39    4-Br  CH.sub.3 3-CF.sub.3                                   3.23(d, 3H), 5.57(s, 1H), 6.87˜                                   8.40(m, 7H), 10.00(s, 1H)    40    4-OCH.sub.3                CH.sub.3 2-CF.sub.3                                   3.20(s, 3H), 3.87(s, 3H), 6.03                                   (s, 1H), 6.53˜8.28(m, 7H),                                   10.37(s, 1H)    41    4-OCH.sub.3                CH.sub.3 3-CF.sub.3                                   3.23(d, 3H), 3.85(s, 3H), 5.60                                   (s, 1H), 6.45˜8.23(m, 7H),                                   10.43(s, 1H)    42    4-OCH.sub.3                CH.sub.3 2-Cl      3.17(s, 3H), 3.90(s, 3H), 6.06                                   (s, 1H), 6.56˜8.17(m, 7H),                                   10.34(s, 1H)    43    4-OCH.sub.3                CH.sub.2 CH═HCl                         2-Cl      3.90(s, 3H), 4.30(q, 2H), 6.10                                   (s, 1H), 6.06, 6.26(m, 2H),                                   6.60˜8.23(m, 7H), 10.07(s,                                   1H)    44    4-OCH.sub.3                CH.sub.3 3-Cl      3.27(s, 3H), 3.90(s, 3H), 5.90                                   (s, 1H), 6.94˜8.23(m, 7H),                                   10.37(s, 1H)    45    4-OCH.sub.3                CH.sub.2 CH═CHCl                         3-Cl      3.87(s, 3H), 4.33(q, 2H), 5.55                                   (s, 1H), 6.15˜6.20(m, 2H),                                   6.57˜8.12(m, 7H), 10.70(s,                                   1H)    46    4-OCH.sub.3                CH.sub.3 2,4-Cl.sub.2                                   3.24(d, 3H), 3.90(s, 3H), 6.07                                   (s, 1H), 6.64˜8.26(m, 6H),                                   10.56(s, 1H)    47    4-OCH.sub.3                CH.sub.2 CH═CHCl                         2,4-Cl.sub.2                                   3.90(s, 3H), 4.28(q, 2H), 6.10                                   (s, 1H), 6.07, 6.28(m, 2H),                                   6.64˜8.25(m, 6H), 10.75(s,                                   1H)    48    4-OCH.sub.3                CH.sub.2 CH═CHCl                         3-CF.sub.3                                   3.25(s, 3H), 3.90(m, 2H),                                   5.50(s, 1H), 6.60(m, 2H),                                   7.25˜8.33(m, 7H), 10.44(s,                                   1H)    49    4-OCH.sub.3                CH.sub.3 3,5-Cl.sub.2                                   3.86(s, 3H), 4.33(s, 3H), 5.57                                   (s, 1H), 6.10˜8.30(m, 6H)    50    4-OCH.sub.3                CH.sub.2 CH═CHCl                         3,5-Cl.sub.2                                   3.28(s, 3H), 3.92(m, 2H),                                   5.58(s, 1H), 6.20(m, 2H),                                   6.48˜8.28(m, 6H)    51    4-NO.sub.2                CH.sub.3 2-CF.sub.3                                   3.15(d, 3H), 6.00(s, 1H), 6.93˜                                   8.62(m, 7H), 10.17(s, 1H)    52    4-SCH.sub.2 CH.sub.3                CH.sub.3 2-CF.sub.3                                   1.40(t, 3H), 3.10(q, 2H), 3.20                                   (s, 3H), 6.05(s, 1H), 6.83˜                                   8.55(m, 7H), 10.43(s, 1H)    53    4-SCH.sub.2 CH.sub.3                CH.sub.3 3,4-Cl.sub.2                                   1.37(t, 3H), 3.06(q, 2H), 3.25                                   (s, 3H), 5.57(s, 1H), 6.87˜                                   8.44(m, 6H), 10.40(s, 1H)    54    4-SCH.sub.2 CH.sub.3                CH.sub.3 3-Cl      1.40(t, 3H), 3.07(q, 2H), 3.28                                   (s, 3H), 5.58(s, 1H), 6.87˜                                   8.40(m, 7H)    55    4-SCH.sub.2 CH.sub.3                CH.sub.2 CH═CHCl                         3,4-Cl.sub.2                              138˜139                                   1.37(t, 3H), 3.06(q, 2H),                                   4.38(m, 2H), 5.58(s, 1H),                                   6.33(m, 2H), 6.82˜8.44(m,                                   6H), 10.60(s, 1H)    56    4-SCH.sub.2 CH.sub.3                CH.sub.2 CH═CHCl                         3-Cl      1.37(t, 3H), 3.07(q, 2H),                                   4.33(m, 2H), 5.57(s, 1H),                                   6.33(m, 2H), 6.38˜8.40(m,                                   7H), 10.67(s, 1H)    57    4-SCH.sub.2 CH.sub.3                CH.sub.3 2,4-Cl.sub.2                                   1.40(t, 3H), 3.17(q, 2H),                                   3.23(s, 3H), 6.06(s, 1H),                                   6.73-8.47(m, 6H),                                   10.40(s, 1H)    58    4-SCH.sub.2 CH.sub.3                CH.sub.2 CH═CHCl                         2-Cl      1.40(t, 3H), 3.13(q, 2H),                                   4.31(m, 2H), 5.93(s, 1H),                                   6.40(m, 2H), 6.87˜8.56(m,                                   7H), 10.66(s, 1H)    59    4-SCH.sub.2 CH.sub.3                CH.sub.3 3-CF.sub.3                                   1.40(t, 3H), 3.13(q, 2H),                                   3.30(s, 3H), 5.73(s, 1H),                                   6.93˜8.50(m, 7H), 10.47(s,                                   1H)    60    6-CH.sub.3                CH.sub.2 CH═CHCl                         4-Cl      2.47(s, 3H), 4.33(m, 2H),                                   5.50(s, 1H), 6.15(m, 2H),                                   6.80˜8.27(m, 7H),                                   10.77(s, 1H)    61    6-CH.sub.3                CH.sub.3 2-CF.sub.3                                   2.63(s, 3H), 3.28(s, 3H),                                   6.30(s, 1H), 6.90˜8.45(m,                                   7H), 10.40(s, 1H)    62    6-CH.sub.3                CH.sub.3 2-Cl      2.50(s, 3H), 3.27(d, 3H),                                   6.66(s, 1H), 6.77˜8.37(m,                                   7H), 10.33(s, 1H)    63    6-CH.sub.3                CH.sub.2 CH═CHCl                         2-Cl      2.43(s, 3H), 4.17(m, 2H),                                   5.93(s, 1H), 6.10˜8.27(m,                                   7H), 10.60(s, 1H)    64    6-CH.sub.3                CH.sub.3 2,4-Cl.sub.2                                   2.46(s, 3H), 3.13(d, 3H), 5.93                                   (s, 1H), 6.73˜8.30(m, 6H),                                   10.37(s, 1H)    __________________________________________________________________________

The process for preparing the above compound of formula(I) according tothe present invention may be further illustrated by the followingexamples, but the present invention is not limited by the examples.

EXAMPLE 1 2-Cyanomethyl-4-methylpyridine

2,4-Lutidine-1-oxide (10 g, 8.10 mmol) was dissolved in anhydrousdioxane (125 ml) under nitrogen atomsphere, and herein p-toluenesulfonylchloride (31.5 g, 162 mmol) was added and refluxed for 5 hours. Thesolution was neutralized with the saturated aqueous solution ofpotassium carbonate and extracted twice with methylene chloride. Thecombined organic layers were dried over anhydrous magnesium sulfate,filtered and concentrated under reduced pressure to get crude product.The residue was separated and purified by column-chromatography oversilica gel to obtain 2-chloromethyl-4-methylpyridine (4.18 g,yield=36%).

2-chloromethyl-4-methylpyridine (3.70 g, 2.17 mmol) was dissolved indimethyl sulfoxide (9 ml) and herein potassium cyanide (1.70 g, 2.60mmol) was added. After stirring for 17 hours at room temperature, waterwas added and it was extracted twice with diethyl ether. The combinedorganic layers were dried over anhydrous magnesium sulfate, andconcentrated under reduced pressure to get crude product. The residuewas separated and purified by column-chromatography over silica gel toobtain the desired product (3.19 g, yield=95%).

EXAMPLE 22-(o-Chlorophenyl)-3-oxo-4-(4-methylpyridyl)-5-amino-2,3-dihydrofurane

Sodium (0.35 g, 15.2 mmol) was added in methanol (8 ml) and stirred atroom temperature under nitrogen atomsphere till complete dissolution ofsodium, and then 2-cyanomethyl-4-methylpyridine (1.10 g, 8.51 mmol) and2-(o-chlorophenyl)2-hydroxymethylacetic acid (1.78 g, 1.35 mmol) wereslowly added. After refluxing for 2 hours with stirring the solution wascooled with a small amount of water and concentrated under the reducedpressure. The residue was extracted with methylene chloride and thecombined organic layers were dried over anhydrous magnesium sulfate,filtered and concentrated under reduced pressure to get crude product.The residue was separated and purified by column-chromatography oversilica gel to obtain the desired product (0.54 g, yield=28%).

EXAMPLE 32-(o-Chlorophenyl)-3-oxo-4-(4-methylpyridyl)-5-methylamino-2,3-dihydrofuran(Compound No. 18)

Solid sodium hydroxide(180 mg, 4.50 mmol) was dissolved in a smallamount of water and then added to methylene chloride (8.6 ml) containing2-(o-chlorophenyl)-3-oxo-4-(4-methylpyridyl)-5-amino-2,3-dihydrofuran(400mg, 1.3 mmol). Tetrabutylammonium bromide (50.0 mg, 1.37 mmol) was addedand then a mixture containing dimethyl sulfate (164 mg, 1.30 mmol) wasslowly added at room temperature. The mixture was stirred at roomtemperature for one hour and then washed twice with water, dried overanhydrous magnesium sulfate. The solvent was evaporated in vacuo toyield a crude product, which was separated by column-chromatography oversilica gel to obtain the desired product (370 mg, yield=88%) as a whitesolid.

Only process for preparing compound No. 18 according to the presentinvention was written in the above examples, but other compoundsaccording to the present invention may be easily prepared by skilledperson in the art.

According to the present invention, 3(2H)-furanone derivative preparedby the above example may be used by itself as agricultural andfloricultural fungicide and also prepared as preparation such as powder,wetting powder, emulsifying condensate, granules, pellets, etc. bymixing with common carrier, interfacial active agent, dispersing agentor comaterials.

The fungicidal activities of 3(2H)-furanone derivatives of theformula(I) according to the present invention prepared by the aboveexamples were tested as followings; wherein all of the test chemicalswere readily dispersed in a standard formulation of acetone in water anda surfactant. In order to test protective effect against plant fungi fornovel compound of the formula(I) according to the present invention 10ml of acetone containing 25 mg of the compound of formula(I) was dilutedin 90 ml of Tween-20 solution producing 250 ppm or 500 ppm solution ofthe compound of above example. And, 50 ml of this chemical solution wassprayed to the foliages of plants. The sprayed plants were left for 24hours at room temperature, and solvent and water were sprayed to applythe following test fungi. Two pots of plants were duplicately tested forfungicidal activity, respectively.

TEST 1 Fungicidal Effect on Rice Blast

Fungal isolates of Pyricularia oryzae were inoculated on rice polishagar media (20 g rice polish, 10 g dextrose, and 15 g agar in 1 ldistilled water) and incubated at 26° C. for 2 weeks. Sporulation wasinduced in a fluorescent light-illuminated incubator at 25°˜28° C.following aerial mycelia were removed from the media by scrapping with arubber spetular. The spores were harvested with sterile distilled waterand adjusted to the concentration of 10⁶ spores/ml. Then the sporesuspension was sprayed to rice blast-susceptable rice plants (Nakdongcultivar) which were already treated with test compounds until justbefore runoff at the stage of 3 or 4 leaves. The inoculated plants wereplaced in a humidity chamber in darkness at 25° C. for 24 h andtransferred to a growth chamber maintained at 26°±2° C. under>90%relative humidity. Five days after the inoculation, disease severity wasdetermined as an area of lesion with the fully expanded leaf which wasthe second leaf from the top of 3- or 4-leaves plants. The lesion areaswere compared with RCB standard rating diagram.

TEST 2 Fungicidal Effect on Rice Sheath Blight

Rhizoctonia solani AG-1 were grown in potato dextrose agar media for 3days and the agar discs were transferred to the Erlnmeyer flask withsterilized wheat bran. After 7 days of incubation, the fungal myceliawere harvested with sterile distilled water and homogenized using Waringblender. The rice plants were inoculated at the stage of 2- or 3- withthe homogenates and placed in a humidity chamber in darkness at 28°±1°C. for 48 h. The plants were transferred to a growth chamber maintainedat 26°±2° C. under>80% relative humidity. Disease severity wasdeterermined at 5 days after the inoculation. Lesion areas wereexpressed as percentages of the lesioned sheath area to the total sheatharea. The values for disease severity were obtained from RSB standardrating diagram.

TEST 3 Fungicidal Effect on Cucumber Gray Mold

Botrytis cinerea KCl isolated from cucumber were inoculated on PDA mediaand incubated at 25° C. for 7 days under dark condition. Sporulation wasinduced in an incubator under 16 h, 25° C. light and 8 h, 20° C. darkconditions for 7 days, the spore harvest was performed as followingsteps; i.e., addition of 10 ml sterile distilled water into the plate,scrapping the spores with a paintbrush, and filtering the sporesuspension through 4 layers of cheesecloth. The concentration of theharvested spore suspension was adjusted to 10⁶ spores/ml. Following thefirst true leaves of cucumber plants were inoculated with the sporesuspension, the plants were placed in a humidity chamber at 20° C. for 5days. Disease severity on the first ture leaves of plants wereevaluated.

TEST 4 Fungicidal Effect on Tomato Late Blight

Phytophthora infestans KA2 were inoculated on V-8 juice agar (200 ml V-8juice, 4.5 g CaCO, 1.5 g agar, 800 ml distilled watr) and incubatedunder 16/8 light/dark photoperiod conditions at 20° C. for 2 weeks. Thesporangia were harvested as same manners in Test 3. The concentration ofthe harvested spore suspension was adjusted to 10⁵ spores/ml, thesporangium suspension sprayed to the tomato plants at the stage of twotrue leaves. The plants were placed in a humidity chamber at 20° C. for4 days under>80% relative humidity. Disease severity on the first andsecond true leaves of plants were evaluated.

TEST 5 Fungicidal Effect on Wheat Leaf Rust

Puccinia recondita were subcultured on wheat plants in a laboratory. Forevaluating fungicidal effect, seeds of wheat plants were planted to 6.5cm-diameter plastic pots. Each pot contained 5 seeds. Seven-day-oldplants with one true leaf were applied with the spores. The inoculatedplants were incubated in a humidity chamber at 20° C. for 24 h and thentransferred to a growth chamber at 20° C. under 70% relative humidity.Disease severity was determined as a percentage of lesion area at 10days after the inoculation.

TEST 6 Fungicidal Effect on Barley Powdery Mildew

Erysiphae graminis f. sp. hordei were subcultured on wheat plants in alaboratory. For evaluating fungicidal effect, seeds of barley plants(Dongboree cultivar) were planted to 6.5 cm-diameter plastic pots. Eachpot contained 15 seeds. Seven-day-old plants with one true leaf wereapplied with the spores. The inoculated plants were incubated in agrowth chamber at 22°˜24° C. under 50% relative humidity. Diseaseseverity was determined as a percentage of lesion area at 7 days afterthe inoculation.

Control values for Test 1˜6 were calculated with the following equation.The results were presented in Table 2. ##EQU1##

                                      TABLE 2    __________________________________________________________________________    Compound          Concen-                Control Value (%)    No.   tration (ppm)                RCM.sup.(1)                    RSB.sup.(2)                        CGM.sup.(3)                            TLB.sup.(4)                                WLR.sup.(5)                                    BPM.sup.(6)    __________________________________________________________________________    15    500   97  100 98  88  67  88    18     50   96  15   0   0  0    0    22    500   0    6  92  20  0   20    23    500   57  38  90   0  0    0    25    500   0   38  88  37  0   23    26    500   89   0  99   0  0    4    26    250   --  --  97  --  --  --    29    500   0   20  96  48  0   21    32    500   0    0  92  13  0   27    34    500   99   0  92  15  0   36    34    250   68  --  96  --  --  --    43    500   60  58  96   0  0    4    44    500   0   30  96  13  14   9    45    500   0   25  98   0  0    3    47    500   0    0  88  16  0   30    53    500   0   11  94  33  0   39    55    250   0    0  100  3  0   25    57    500   0    5  94  10  0   31    61    500   0   21  96  72  0   23    __________________________________________________________________________     .sup.(1) RCM: Rice Blast     .sup.(2) RSB: Rice Sheath Blight     .sup.(3) CGM: Cucumber Gray Mold     .sup.(4) TLB: Tomato Late Blight     .sup.(5) WLR: Wheat Leaf Rust     .sup.(6) BPM: Barley Powdery Mildew

What is claimed is:
 1. A compound of 3(2H)-furanone having the followingformula(I) ##STR6## wherein, R is C₁ ˜C₂ alkyl, allyl or 2-chloroallylgroup;X is halogen atom, methyl, C₁ ˜C₂ alkoxy, cyano, thioethyl ornitro group; and Y is halogen atom, hydrogen, methyl or trifluoromethylgroup.
 2. The compound of 3(2H)-furanone according to claim 1, wherein Ris methyl group, X is methyl group and Y is chlorine atom.
 3. Afungicidal composition comprising one or more compounds of formula(I) asan effective ingredient in combination with an inert carrier; ##STR7##wherein, R, X and Y are respectively defined as the above claim
 1. 4. Aprocess for preparing compounds of formula(I) which comprises thefollowing steps;reacting N-oxide compound of the following formula(II)with p-toluenesulfonyl chloride and heating the solution; preparingmethylcyanopyridine of the following formula(III) by adding dimethylsulfoxide and potassium cyanide and reacting at room temperature;preparing aminofuranone compound of the following formula(V) by reactinghydroxymethylaromatic acid ester compound of the following formula(IV)in the presence of a base catalyst; and introducing a correspondingsubstituent at the position of amino group of the formula(V) in thepresence of a phase transfer catalysts; ##STR8## wherein, R, X and Y arerespectively defined as the above claim
 1. 5. The process for preparinga compound of 3(2H)-furanone according to claim 4, wherein said basecatalyst is sodium methoxide and said phase transition catalyst istetrabutylammonium bromide.